68505-92-0

Usage

InChI:InChI=1/C11H13ClN2O3/c1-2-3-6-13-11(15)9-7-8(14(16)17)4-5-10(9)12/h4-5,7H,2-3,6H2,1H3,(H,13,15)

Upstream product

• 25784-91-2 2-chloro-5-nitrobenzoylchloride 
• 109-73-9 N-butylamine 
• 2516-96-3 2-chloro-5-nitrobenzoic acid 
• 3858-78-4 n-butylamine hydrochloride 

Downstream Products

• 130653-38-2 N-Butyl-5-nitro-2-propylamino-benzamide 
• 85469-88-1 N-Butyl-2-isobutoxy-5-nitro-benzamide 
• 68505-93-1 N-Butyl-5-nitro-2-(2-propynyloxy)-benzamide 
• 130653-41-7 N-Butyl-2-butylamino-5-nitro-benzamide 
• 130653-35-9 N-Butyl-2-methylamino-5-nitro-benzamide 
• 85469-89-2 2-Benzyloxy-N-butyl-5-nitro-benzamide 
• 400039-33-0 2-p-fluorophenyloxy-5-nitro-N-butylbenzamide 
• 355375-33-6 2-p-chlorophenyloxy-5-nitro-N-butylbenzamide 
• 96206-50-7 N-butyl-2-cyclohexyloxy-5-nitro-benzamide 
• 96206-55-2 2-phenyloxy-5-nitro-N-butylbenzamide 
• 891184-55-7 N-butyl-2-p-tolyloxy-5-nitrobenzamide 
• 1395396-12-9 N-butyl-2-p-trifluoromethylphenoxy-5-nitrobenzamide 
• 1395396-15-2 N-butyl-2-o-trifluoromethylphenoxy-5-nitrobenzamide 
• 1395396-01-6 N-butyl-2-(adamantan-1-yloxy)-5-nitrobenzamide 

Relevant academic research and scientific papers

Synthesis of benzamide derivatives and their evaluation as antiprion agents

A new set of 5-(2-(pyrrolidin-1-yl)acetamido)-N-butyl-2-(substituted) benzamide and 5-(2-(piperidin-1-yl)acetamido)-N-butyl-2-(substituted) benzamide derivatives were synthesized in which as structural features the 2-(1-pyrrolidinyl)- or 2-(1-piperidyl)acetylamino group or a diphenylether moiety are associated to a benzamide scaffold. Their binding affinity for human PrPC and inhibition of its conversion into PrPSc were determined in vitro; moreover, the antiprion activity was assayed by inhibition of PrPSc accumulation in scrapie-infected mouse neuroblastoma cells (ScN2a) and scrapie mouse brain (SMB) cells. The results clearly indicate the benzamide derivatives as attractive lead compounds for the development of potential therapeutic agents against prion disease.

In vitro mutagenicity of?anti-inflammatory parsalmide analogues PA7, PA10, and?PA31 triggered by?biotransformation into hydroxy derivatives

In this study, the mutagenicity of the anti-inflammatory parsalmide [5-amino-N-butyl-2-(2-propynyloxy)-benzamide] analogues PA7 [5-amino-N-butyl-2-cyclohexyloxy-benzamide], PA10 [5-amino-N-butyl-2-phenoxy-benzamide] and PA31 [5-amino-N-butyl-2-(p-tolyloxy)-benzamide] was determined by an Ames Salmonella assay. The experiments were performed by preincubating the compounds in the absence and presence of a post-mitochondrial fraction (S9) of rat liver homogenate from phenobarbital/β-naphtoflavone treated rats. No mutagenic effect was observed after direct testing (no S9 added) in Salmonella typhymurium strains TA98, TA100, TA102, TA1535 and TA1537. However, in the presence of S9, the test substances triggered mutagenic responses in strains TA100 and TA98. PA31 presented the strongest mutagenic potential. The reversion rates in the presence of PA31 were about 2-19 fold higher than spontaneous mutation rates. In the presence of PA7, the reversion increased 2-14-fold over spontaneous rates. While PA10 showed a relatively mild mutagenic potential, as the number of revertants did not exceed 2.5 times the number of spontaneous mutations. Mass spectrometric analysis of the in vitro biotransformation showed that S9 converted (%), regioselectively, PA7 (19%), PA10 (7%) and PA31 (12%) into hydroxy-derivatives.

Synthesis of substituted benzamides as anti-inflammatory agents that inhibit preferentially cyclooxygenase 1 but do not cause gastric damage

Parsalmide (5-amino-N-butyl-2-(2-propynyloxy) benzamide) (5a), is a non-steroidal anti-inflammatory drug (NSAID), commercialised in Italy until 1985 with the brand name of Synovial, that has been widely used to treat arthritic patient. In addition, it was shown to spare gastric mucosa. Here we have synthesised a series of novel substituted benzamides, related to Parsalmide, and have evaluated their activity in vitro on COX-1 and COX-2 as well as in vivo in the carrageenin-induced rat paw edema, a classical in vivo anti-inflammatory assay. Compounds 5b, 11a and 11b, which showed a favourable profile in vitro and in vivo, were screened in comparison with Parsalmide for gastrointestinal (GI) tolerability in vivo in the rat. Results obtained showed that Parsalmide and compound 11b inhibited both COX-1 and COX-2 in vitro as well as they were active in vivo. Both compounds were devoid of gastric effect at the efficacious dose. In addition, both prevented indomethacin-induced gastric damage. Thus, these compounds may guide the definition of a new leading structure with anti-inflammatory activity that may allow designing new safer NSAIDs.